Two different strategies for the synthesis of pentacyclic Strychnos alkaloids in enantiomerically pure form are explored. Both of them involve the use of enantiopure 2-(4-piperidylmethyl)indoles prepared by kinetic resolution of l-(3-pyridyl)ethanol, followed by partial reduction of the pyridine rin
First total synthesis and NMR data of the Strychnos alkaloid 19,20-dihydroakuammicine
β Scribed by Mercedes Amat; Ana Linares; Joan Bosch
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 232 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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Total Syntheses of the Strychnos Indole Alkaloids (-)-Tubifoline, (-)-Tubifolidine, and (-)-19,20-Dihydroakuammicine. -The key steps in the synthesis of the title compounds (X), (XI), and ( XIII) are kinetic resolution of the racemic alcohol (I), orthoester Claisen rearrangement to the ester (IV), s
The total synthesis of3 the %z&no~ indole alkaloid tubifoline and detailed H-and C-NMR data of thisalkaloid are reported. ## Tubifoline is a pentacyclic Stigchao~ indole alkaloid, 1 having the Strychnan skel-eta1 type, whose isolation and structural elucidation were reported by Schmid in 1964. 2
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